Why Your Strategy Day Doesn’t Work
(and What to Do Instead)

You’ve booked the venue, cleared calendars, and spent days preparing slides. On the day, the senior leadership are energised, ideas flow, and everyone leaves inspired. Fast-forward three weeks, and nothing’s changed.

That’s because most strategy days fail not from lack of ambition, but from lack of rhythm. A strategy day is an event. Strategy itself is a system – one built through cadence, accountability, and connection.

If strategy isn’t part of your leadership routine, it becomes theatre: something you perform once a year, applaud, and forget.

As a business growth consultant, I see this pattern constantly: leaders want transformation but forget that discipline drives results. The difference between a plan and a business growth strategy is rhythm.

Why Strategy Days Don’t Deliver

Most offsites miss the mark because:

• They’re stand-alone. One big day, then business as usual.
• They lack cadence. Without consistent follow-up, good intentions evaporate.
• They’re too safe. When the CEO runs the session, who’s going to disagree? (Exactly.)
• They confuse ideas for execution. A 20-page slide deck is not a growth plan.

If your facilitator is the same person who approves your budget, you don’t have a business strategy workshop – you have a compliance meeting.

The Coach, Not the Captain

That’s why your facilitator should be your business coach – an independent guide who helps you and your team think deeply, challenge safely, and stay accountable beyond the room. Coaching gives leaders space to reflect, test ideas, and reconnect to the “why” behind the business.

The best leaders I work with treat strategy like fitness: a weekly discipline, not an annual detox. In my executive coaching work, this rhythm creates the consistency that builds freedom, capability, and performance.

This is where business consulting meets leadership coaching – it’s not about advice, it’s about systems that make progress inevitable.

Time to Retire the SWOT

Let’s be honest, most SWOT analyses are a comfortable chat about what everyone already knows. Instead, spark creativity by looking outward:

• What could your team learn from hospitality about customer experience?
• What could tech teach you about speed and iteration?
• How do the best global brands make their strategy rhythms visible and alive?

Innovation often hides in other industries – not in your spreadsheet. The best business consultancies help clients look outward, not inward, to find their next leap.

Build a System, not a Session

High-performing businesses use strategy rhythm, not one-off bursts. The winning pattern looks like this:

• Quarterly planning workshops to align with a clear three-year Vivid Vision and business roadmap.
• Monthly leadership check-ins to track progress, tackle bottlenecks, and grow capability together.
• Weekly huddles that make accountability normal, not personal “What moved? What’s next?”
• Ongoing coaching for CEOs, so they stay strategic, not stuck in the day-to-day.

When that rhythm becomes habit, strategy stops being “extra work” and becomes how work gets done.

Start with Focus – The #1 Addressable Challenge

Every effective strategy rhythm starts with clarity – and that means identifying your number one addressable challenge. It’s the single issue or opportunity that, if solved, will create the biggest impact for the business in the next period.

The key is in the word addressable – something you can influence, not just observe. It becomes the through-line for your leadership rhythm:

• In quarterly planning, it shapes the focus of your strategic sprints.
• In monthly reviews, it keeps everyone accountable to what matters most.
• In weekly huddles, it anchors discussion on progress, barriers, and next steps.

Focusing on one addressable challenge brings alignment, shared ownership, and momentum – it turns meetings into movement.

(I’ll unpack how to define and use your #1 Addressable Challenge which is a term coined by my friend and fellow coach Mark Green, in next week’s article – and share a few client examples from business growth strategy that lifted profitability, execution, and leadership alignment.)

The Leadership Multiplier™ in Action

Strategy only scales when leadership does. The Leadership Multiplier™ – from driver to multiplier is about growing others, not just driving outcomes yourself. It’s the shift from telling to teaching, from doing to developing, and from leading meetings to leading momentum.

Leaders who coach create capacity; leaders who control create dependency. This is where business growth consulting and leadership coaching combine to scale performance sustainably.

As You Head into the New Year

So, as you approach annual planning, pause for a moment and ask:

• What will make this year different?
• What will it mean for you as a leader to truly empower others, not carry them?
• How can your team normalise strategic focus and accountability – where it’s just “how we do things around here”?
• How will your business show up as a valued partner, not just another supplier?

If you want your next strategy workshop to actually work, stop treating it as a presentation and start treating it as practice. Because growth isn’t built in bursts – it’s built in rhythm.

Final thought:

The best strategy days don’t end with applause – they end with alignment, commitment, and the first step of a rhythm that keeps you honest all year.

So, before you book the venue again… ask yourself – who’s facilitating your next strategy workshop: your CEO, or your business coach?